Ethyl oleate

BP Ethyl oleate PhEur Ethylis oleas USPNE Ethyl oleate 

Ethyl 9-octadecenoate Kessco EO oleic acid, ethyl ester. 

Ethyl oleate is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration. It has also been used as a solvent for drugs formulated as biodegradable capsules for subdermal implantation and in the preparation of microemulsions containing cyclosporin.  

Ethyl oleate is a suitable solvent for steroids and other lipophilic drugs. Its properties are similar to those of almond oil and peanut oil. However, it has the advantage that it is less viscous than fixed oils and is more rapidly absorbed by body tissues.  

Ethyl oleate has also been evaluated as a vehicle for subcutaneous injection.  

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In some compositions the PIB is plasticized with ethyl oleate to improve low temp properties. .. Since the propint is a stiff paste it can be inserted into a rocket motor by a type of injection moulding process (Refs 3 5)... 

The Analysis of Ethyl Oleate and Its Determination in Plastic Propellant and Propellant Premixes by Gas Chromatography , Rept No QAD (MATS 1-166 (Engl) (1970)... 

The search for solvents led to the discovery that sodium borohydride is an excellent reducing agent for aldehydes and ketones. The search for catalysts to enhance the reducing power of sodium borohydride led to an anomalous result in the reduction of ethyl oleate. Investigation of this anomalous result led to the discovery of hydroboration. 

Certain small-volume injections are available where the dmg is dissolved in a viscous oil because it is insoluble in water non-aqueous solvent must be used, hi addition, drags in non-aqueous solvents provide a depot effect, for example for hormonal compounds. The intramuscular route of injection must be used. The vehicle may be a metabolizable fixed oil such as arachis or sesame oil (but not a mineral oil) or an ester such as ethyl oleate which is also metabolizable. The latter is less viscous and therefore easier to administer but the depot effect is of shorter duration. The dmg is normally dissolved in the oil, filtered under pressure and distributed into ampoules. After sealing, the ampoules are sterilized by dry heat, for example, at 160°C for 2 hours. A bactericide is probably ineffective in such a medium and therefore offers very httle protection against contamination in a multidose oily injection. 

Larva Stimulate development of worker hypo-pharyngeal glands Ethyl oleate 90 methyl palmitate 78 [148]... 

Ethyl nipecotate, e249 Ethyl oleate, e230 Ethyl oxirane, e3... 

Microwave-assisted (0.1 or 0.2 Wg-1) convection drying was also applied to osmotically dehydrated blueberries, leading to dried berries that were comparable to freeze-dried ones in much shorter time (Venkatachalapathy and Raghavan, 1998). Frozen blueberries were also dried in a microwave and spouted bed combined dryer (MWSB) after a pretreatment using ethyl oleate and a NaOH dipping solution followed by sucrose osmotic treatment (Feng et al., 1999). Osmotic dehydration prevented the blueberries from... 

Surface organometallic and related molecular species Propene Ethyl oleate Reference... 

The surface species is an active catalyst for propene metathesis (780 eq., TOI min = 0-89 molpropene hioImo s" for the catalyst obtained by the benzene impregnation route) and ethyl oleate metathesis (lOOeq. TOI mm =0.11 moloieate hioImo s for the catalyst obtained by the benzene impregnation route) [136]. The high catalytic activity of the surface neopentylidene complex has not been modeled by the silsesquioxane analogue [136]. 

Table 14.2 Comparison between silica-supported, silsesquioxane, and molecular Mo(VI) precursor as catalysts for octene and ethyl oleate self-metathesis.

Complete reduction of unsaturated esters to sativated alcohols takes place when the esters are hydrogenated over Raney nickel at 50° and 150-200 atm [44] or over copper chromite at temperatures of 250-300° and pressures of 300-3 50 atm [52,1056] (p. 153). In contrast to most examples in the literature the reduction of ethyl oleate was achieved at atmospheric pressure and 270-280° over copper chromite, giving 80-90% yield of octadecanol [1074]. a.,P-Unsaturated lactones are reduced to saturated ethers or alcohols, depending... 

This procedure is used in pharmacopoeial assays of benzyl benzoate, dimethyl phthalate, ethyl oleate, methyl salicylate, cetostearyl alcohol, emulsifying wax, castor oil, arachis oil, cod liver oil, coconut oil. 

Graciaa A, Lachaise J, Cucuphat C, Bourrel M, Salager JL (1993) Interfacial segregation of ethyl oleate/hexadecane oil mixture in microemulsion systems. Langmuir 9 1473-1478... 

A novel method for production of paraffinic hydrocarbons, suitable as diesel fuel, from renewable resources was illustrated. The fatty acid ethyl ester, ethyl stearate, was successfully converted with high catalyst activity and high selectivity towards formation of the desired product, heptadecane. Investigation of the impact of catalyst reduction showed that the reduction pretreatment had a beneficial effect on the formation of desired diesel compound. The non-pretreated catalyst dehydrogenated ethyl stearate to ethyl oleate. The experiments at different reaction temperatures, depicted that conversion of ethyl stearate was strongly dependent on reaction temperature with Eact=69 kj/mole, while product selectivities were almost constant. Complete conversion of ethyl stearate and very high selectivity towards desired product (95%) were achieved at 360°C. 

Figure .5 Relative biodegradation levels of SBFs positive control (ethyl oleate), intermediate control (hexadecene), negative control (squalane), base oil Rheosyn (LAO),...

Representative esters of oleic add are methyl oleate, C17H33COOCH3, bp 190 C at 10 millimeters pressure ethyl oleate. CnH COOCiHs, bp 205°C at 10 millimeters pressure glyceryl trioleate (triolein), (jj, bp 240°C at 18 millimeters pressure. 

Ethyl nicotinate, e215 Ethyl nipecotate, e205 Ethyl oleate, el 89... 

InLammation by subcutaneous injection of cosolvents has not been published on extensively. Radwan [134] used aim vivo screening model to study the effect of various oils and cosolvents in oils on increasing skin fold thickness of rats after subcutaneous injection. With the exception of benzyl alcohol, ethyl oleate, and phospholipon 100, most excipients showed only miaanihnatory responses. 

Esterification of oleic acid using ethanol to make ethyl oleate... 

The complex WOCI4—Cp2TiMe2 was used for the metathesis of ethyl oleate (51) to give diethyl 9-octadecenedioate (52). Civetone (53) was synthesized by the Dieckmann condensation of this diester, followed by decarboxylation [20], Homometathesis of terminal alkenes is useful, because it yields symmetric internal alkenes and ethylene, which can be removed easily. Metathesis of 10-undecenoate (54) proceeds smoothly to give the diester 55 [20],... 

In order to increase the sustainability of chemical processes, environmentally friendly solvents such as supercritical fluids (SCFs) are widely investigated. Han and coworkers studied the ethenolysis of ethyl oleate in SC C02 in relation with the phase behavior of the reaction mixture [62]. They carried out the ethenolysis reaction at 35°C in the absence of C02 and in the presence of C02 at three different pressures (50, 82, and 120 bar). The reaction in the absence of C02 reached equilibrium in 1 h at 80% conversion. The reaction rate in the presence of 50 bar of C02 was higher than without C02 and, at 82 bar, again increased with respect to 50 bar. However, when the pressure was increased to 120 bar, the reaction rate decreased. This effect was explained according to the variations on the phase behavior with the pressure an increase in the C02 pressure carried an increase of solubility of reactants, products, and C02, which produced a decrease of the viscosity of the reaction mixture. This positive effect was enhanced at 82 bar and was accompanied by an increase of selective solubility of the products in the vapor phase that further increased both reaction rate and conversion. The decrease of efficiency at 120 bar was related to an increase of the solubility of the reactants in the C02 phase. 

The catalyst system [Rh(acac)(CO)2]/biphephos shows high activity for isomerization with yields of 60% of branched isomers at 20 bar CO/H2 pressure and 115°C [10]. With this catalyst system, a 26% selectivity of linear aldehyde from ethyl oleate was observed. The selectivity for the n-aldehvde was higher at 34% for linoleic acid. A hydrogenation side product was observed in the reaction due to the isomerization of the double bond toward the ester group, where hydrogenation is favored. 

A rhodium catalyst [Rh(cod)Cl]2 was applied at 140°C and 100 bar to achieve a yield of 99% in hydroaminomethylation of ethyl oleate and morpholine. Several amines were tested in the reaction with fatty compounds hexylamine, benzylamine, aspartic diethyl acid, valinol, and diisopropylamine are further amines which can be employed in hydroaminomethylation. The conversion with primary amines showed that hydroaminomethylation can proceed twice on the amine. The dimer fatty acid ester bridged with an amine is a highly functionalized molecule with various applications. An excess of the primary amine during the reaction prohibits the reaction of the hydroformylation product with a secondary amine which is the product of hydroaminomethylation with the primary amine (Scheme 19). 

Scheme 19 Hydroaminomethylation of ethyl oleate with a primary amine...

The products of lipid oxidation in monolayers were also studied. Wu and coworkers (41) concluded that epoxides rather than hydroperoxides might be the major intermediates in the oxidation of unsaturated fatty acids adsorbed on silica, presumably because of the proximity of the substrate chains on the silica surface. In our work with ethyl oleate, linoleate and linolenate which were thermally oxidized on silica, the major decomposition products found were those typical of hydroperoxide decomposition (39). However, the decomposition patterns in monolayers were simpler and quantitatively different from those of bulk samples. For example, bulk samples produced significantly more ethyl octanoate than those of silica, whereas silica samples produced more ethyl 9-oxononanoate than those of bulk. This trend was consistent regardless of temperature, heating period or degree of oxidation. The fact that the same pattern of volatiles was found at both 60°C and 180°C implies that the same mode of decomposition occurs over this temperature range. 

Oleyl alcohol has been previously prepared only by the reduction of ethyl oleate with sodium and absolute ethyl alcohol.1 By substituting butyl alcohol for ethyl alcohol, the procedure is less time-consuming and less dangerous to carry out, and gives better yields. 

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